Mercapto-thiazole derivatives



Patented 14.11.25, 1938 UNITED STATES PATENT OFFICE MnncAP'ro-Tnmzonn DERIVATIVES Ludwig Orthner', Frankfort-on-the-Main, and Ewald Zaucker, Cologne-Mulheim, Germany, assignors to I. G. Farbenindustrle Aktiengesellschaft, Frankfort-on-the-Main, Germany No Drawing, Original application June 23, 1931,

Serial No. 546,418.

many June 30, 1930 15 group linked to the C are replaced by the group wherein R. stands for a benzene or naphthalene radical. As examples for substituents in the said benzeneor naphthalene nuclei there may be 25 mentioned alkyl, alkoxy or nitro groups or halogen atoms.

These new compounds are obtainable by causing an about molecular quantity of a monoor dihalogen acetamide to react upon about one 30 molecular proportion of a mercaptoarylene thiazole or a salt thereof per each halogen atom. As suitable halogenated acetamides there may be mentioned, for instance, dichloroacet-amide:

35 CHCI2.CO.NH2; N-dlchloro-acet-piperidide:

l. is

dichloro-acet-anilidez CHC12.CO.NH.COH; N-di-.

45 chloro-acetyl-anthranilic acid ester:

CHCh.CO.NI-I.CuH4.COOC2I-Is; dichloroacetyl-dimethylamide CHCI:.CO.N(CH;)2;

Divided and this application August "I, 1935, Serial No. 35,064.

In Ger- & 2 Claims. (Cl. 260-44) dichloroacetyl-dibutylamide: I v

' CHCIZ.CO.N(C4HI)2;

dichloroacetyl-dibenzylamide: 5

CHC12.CO.N(CH2.CcHs) a; I

as.dichloroacetyl-phenylhydrazide:

CHC12.C 0.NH.NH.CcH5;

as.dichloro-aceto-ortho-nitrophenylhydrazide:

CHCI2.CO.N'H.NH.CsH4.NOa; l

' dichloro-acetylpropylamide: CHC12.CO.NH.C3H7.

' The new compounds are generally colorless to yellowish colored crystalline substances, insoluble in water, soluble in the usual organic solvents, and are particularly valuable in view of their favorable critical temperatures, when applied in the vulcanization of rubber or of artificial rubberlike masses.

Fonvulcanization purposes the new compounds are incorporated within the rubber (which term is intended to include natural rubber as well as artificial rubber-like masses, derived for example,

from butadiene, isoprene, dimethylbutadiene or another homologue or an analogue of butadiene) in anydesired manner, for example, by rolling or kneading. Obviously, a vulcanizing agent, such as sulfur, agents'being capable of splitting ofi sulfur, selenium etc., is likewise added, and,

'if desired, other ingredients known to favorably influence rubber vulcanization processes or the properties of the vulcanizates. The rubber mix is then vulcanized in the usual manner by heating it to a temperature suflicient to perform vul- 40 canization, for example, to a temperature between about 100-170" C.

Representatives possessing too low a velocity on hot vulcanization, can be adjusted to give more favorable times of heating by combination with stearic acid and/or with other appropriate accelerators, especially basic accelerators, while preserving a satisfactory critical temperature.

The following examples will illustrate the invention, without, however, restricting it theretoz- I the melting point of 179 C. The reaction probably proceeds according to the equation:

Example 2 In comparison with mercapto benzothlazole (I) the condensation products from mercapto benzothiazole (sodium salt) and dichloroacetamide (II) were tested as accelerators in the following mixture:

' Parts by weight Crepe Zinc oxide a 5 Sulfur 3- Stearic acid.. 1.5

Accelerator The following values were obtained:-

A=tensile strength in kg. per

q- 01 B=stretch in percent.

Heating I 11 Pressure Mlnab.atm. utea A B A B With a mixture of the composition:-- 7

y Parts by weight Crepe- 100 Zing mrirln 5 Sulfur 3 Stearic acid 1.5

and

The reaction product from mercapto benzothiazole (sodium salt) with dichloroacetamide 0. 33

plus Diphenylguanidine (III) 0.67

the followingflgures were obtained:

Heating III Pressure Minnb. atm. utes A B This is a division of our application for Letters Patent Serial No. 546,418, filed June 23, 1931.

We claim:--- 1. As new compounds acetamides in which at the most 2 hydrogen atoms of the methyl group linked to the C0 are replaced by the group wherein R stands for a benzene or naphthalene radical, these compounds being valuable vulca- V nization accelerators;

2. The product of the formula having a melting point of 179 C. and being a valuable vulcanization accelerator.

. 'LUDWIG ORTHNER.

EWALD ZAUCKER. 

